Sequential C−H Borylation and N-Demethylation of 1,1′-Biphenylamines: Alternative Route to Polycyclic BN-Heteroarenes
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Title
- Sequential C−H Borylation and N-Demethylation of 1,1′-Biphenylamines: Alternative Route to Polycyclic BN-Heteroarenes
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Author(s)
- Jianbo Zhang; Hoimin Jung; Dongwook Kim; Sehoon Park; Sukbok Chang
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Subject
- boranes, ; C−H activation, ; heterocycles, ; isosterers, ; reaction mechanisms
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Publication Date
- 2019-05
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Journal
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.58, no.22, pp.7361 - 7365
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Publisher
- WILEY-V C H VERLAG GMBH
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Abstract
- © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Described herein is an unprecedented access to BN-polyaromatic compounds from 1,1′-biphenylamines by sequential borane-mediated C(sp 2 )−H borylation and intramolecular N-demethylation. The conveniently in situ generated Piers’ borane from a borinic acid reacts with a series of N,N-dimethyl-1,1′-biphenyl-2-amines in the presence of PhSiH 3 to afford six-membered amine-borane adducts bearing a C(sp 2 )−B bond at the C2′-position. These species undergo an intramolecular N-demethylation with a B(C 6 F 5 ) 3 catalyst to provide BN-isosteres of polyaromatics. According to computational studies, a stepwise ionic pathway is suggested. Photophysical characters of the resultant BN-heteroarenes shown them to be distinctive from those of all-carbon analogues ⓒ 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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URI
- https://pr.ibs.re.kr/handle/8788114/5980
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DOI
- 10.1002/anie.201902499
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ISSN
- 1433-7851
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Appears in Collections:
- Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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